Phosphorus, Sulfur, and Silicon and the Related Elements, ( ISI ), Volume (190), No (5), Year (2015-6) , Pages (911-917)

Title : ( C═O•••π INTERACTION: A RARE NONCOVALENT BINDING IN RC(O)NHP(O)[NR1R2]2 PHOSPHORIC TRIAMIDE STRUCTURES )

Authors: Mahnaz Rostamichaijan , Mehrdad Pourayoubi , Marek Nečas , Krishnan Damodaran ,

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Abstract

In the structure of C6F5C(O)NHP(O)[N(C2H5)(C6H11)]2, in addition to N—H…O═P hydrogen bond, the oxygen atom of P═O group is involved in the P═O…π interaction (OP…Cg = 3.507(1) Å, Cg is the centroid of C6F5 ring). Moreover, a noncovalent C═O…π interaction takes part in the crystal packing, OC…Cg = 3.159(1) Å. The C═O…π interaction is the interesting feature of this structure, as a Cambridge Structural Database analysis (CSD; Allen, Acta Cryst. 2002, B58, 380–388) of 149 structures with a C(O)NHP(O)[N]2 skeleton shows that such an interaction exists only in 4 structures. The dihedral angle between the aromatic ring and the plane defined by the atoms of [C][N]C═O segment is 66.66◦. The C═O bond length in the present structure (of 1.2148(18) Å) is within the expected range for compounds with a C(O)NHP(O)[N]2 segment; however, due to the electronic effect caused by C6F5 group, it is in the region of the short bond lengths for analogous structures deposited in the CSD (1.18–1.26 Å). The P═O (1.4831(10) Å) and P—N (1.6340(12) Å and 1.6424(12) Å) bond lengths are standard for a phosphoric triamide structure and the P—N bond of C(O)NHP(O) segment (1.6980(12) Å) has an expected longer value relative to the other P—N bonds. The bond-angle sums around the tertiary nitrogen atoms (SUM = 2 × P—N—C + C—N—C) are 357.8° and 352.0° that show few deviations from the planar value of 360°. The more pyramidal N atom is oriented so that the corresponding lone electron pair is anti with respect to the P═O group.

Keywords

CSD; crystal structure; phosphoric triamide; C═O…π
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@article{paperid:1048755,
author = {Rostamichaijan, Mahnaz and Pourayoubi, Mehrdad and Marek Nečas and Krishnan Damodaran},
title = {C═O•••π INTERACTION: A RARE NONCOVALENT BINDING IN RC(O)NHP(O)[NR1R2]2 PHOSPHORIC TRIAMIDE STRUCTURES},
journal = {Phosphorus, Sulfur, and Silicon and the Related Elements},
year = {2015},
volume = {190},
number = {5},
month = {June},
issn = {1042-6507},
pages = {911--917},
numpages = {6},
keywords = {CSD; crystal structure; phosphoric triamide; C═O…π},
}

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%0 Journal Article
%T C═O•••π INTERACTION: A RARE NONCOVALENT BINDING IN RC(O)NHP(O)[NR1R2]2 PHOSPHORIC TRIAMIDE STRUCTURES
%A Rostamichaijan, Mahnaz
%A Pourayoubi, Mehrdad
%A Marek Nečas
%A Krishnan Damodaran
%J Phosphorus, Sulfur, and Silicon and the Related Elements
%@ 1042-6507
%D 2015

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